B-(2-甲基苯并[b]噻吩-3-基)-硼酸 | 881998-67-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 中文名称: B-(2-甲基苯并[b]噻吩-3-基)-硼酸
• 英文名称: (2-methylbenzo[b]thiophen-3-yl)boronic acid
• 英文别名: (2-methyl-1-benzothiophen-3-yl)boronic acid
• CAS: 881998-67-0
• 化学式: C₉H₉BO₂S
• 分子量: 192.046
• InChiKey: VFGACBSDOHKSOK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.89
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  68.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  B-(2-甲基苯并[b]噻吩-3-基)-硼酸 在 四(三苯基膦)钯 、 cesium fluoride 、 potassium hydroxide 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 反应 76.0h， 生成 1,2-bis(2-methylbenzothiophene-3-yl)maleic anhydride
  参考文献：
  名称：

  On the use of diarylmaleimide derivatives in biological contexts: An investigation of the photochromic properties in aqueous solution

  摘要：

  A series of photochromic diarylmaleimide derivatives has been synthesized and studied with respect to the photochromic properties in aqueous solution. The main rationale is to investigate if these compounds could be used as photoswitchable units in biological contexts, motivated by the fact that the diarylmaleimide structural motif is identified in many pharmacophores. Thus, photoswitchable variants of this class of compounds could be very useful in the quest for photoactivatable drugs. The photoinduced cyclization reaction (colorization) is suppressed in solvents of high polarity, whereas the ring-opening reaction (decolorization) still occurs with high efficiency. The photochromically active anti-parallel conformer of the open form is more abundant in the asymmetrically substituted derivatives, which in turn favors the formation of the closed isomeric form. The rates of the thermal isomerization reactions have also been assessed, together with the resistance toward thermal degradation. Here it was observed that the maleimide derived compounds were not susceptible to the thermally driven reactions (hydrolysis and isomerization). (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2016.10.023
• 作为产物：
  描述：

  2-甲基苯并噻吩 在 正丁基锂 、 溴 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 生成 B-(2-甲基苯并[b]噻吩-3-基)-硼酸
  参考文献：
  名称：

  Substituent and solvent effects on the fluorescent and photochromic properties of 2-(2-pyridyl)imidazole containing diarylethene derivatives

  摘要：

  合成并表征了五种以2-(2-吡啶基)咪唑为乙烯桥的二芳乙烯衍生物（PI-BTEs）。PI-BTEs（L1–L5）的结构和性能不仅可以通过噻啉单元进行修改，还可以通过咪唑氮上的取代基进行调整。值得注意的是，用苯并噻吩替代噻啉后，耐疲劳性显著提高，闭合形式的中心吸收带从572 nm（L3）位移到550 nm（L2），溶液的颜色从L3中的浅粉色变为L2中的红紫色。此外，L3在各种溶剂中的斯托克斯位移（Δν）值与溶剂的供体数（DN）和溶剂极性参数Δf表现出良好的线性关系。

  DOI：

  10.1039/c3ra43110j

文献信息

• Imidazole diarylethene switches: an alternative to acid-gated photochromism
  作者：Kang-Tai Xiong、Meng-Lian Li、Yue Jiang、Hai-Bing Xu、Ming-Hua Zeng

  DOI：10.1039/d0nj00606h

  日期：——

  We prepared five diarylethenes containing 2-aryl-imidazole as the ethene bridge (L1–L5), and introduced response sites in imidazole rather than in the traditional appended aryl units to regulate their photochromism and thermal stability under acid stimulus. The results show that we can change the thermal stability from P- to T-type, and prevent their photoactivity by acidification, and it is clarified

  我们准备了五个含有2-芳基咪唑作为乙烯桥（L1-L5）的二芳烃，并在咪唑中而不是在传统的附加芳基单元中引入了响应位点，以调节它们在酸刺激下的光致变色和热稳定性。结果表明，我们可以将热稳定性从P型转变为T型，并通过酸化阻止其光活性，并且可以证明，酸越强或添加的酸越多，二芳基乙烯光稳定性的衰减速度越快。此外，可以通过用等摩尔量的碱中和来恢复被禁止的光活性。
• New photochromic diarylethenes including P and Si atoms
  作者：Lahoussine Bougdid、Andre Samat、Corinne Moustrou

  DOI：10.1039/b901277j

  日期：——

  The preparation of new photochromic diarylcyclopentenes including silicon or phosphorus atom in the pentatomic cycle is described. Starting from butadienes substituted in 2 and 3 positions by thienyl or benzothienyl groups, the targeted molecules have been obtained through a three-step convergent synthesis with relatively good yield. These original structures open a novel area of investigations for this family of compounds which is known for promising applications in the fields of optoelectronic devices and optical memories.

  本文介绍了在五原子循环中包含硅原子或磷原子的新型光致变色二芳基环戊烯的制备方法。从 2 位和 3 位被噻吩基团或苯并噻吩基团取代的丁二烯开始，通过三步会聚合成法获得了目标分子，且收率相对较高。这些新颖的结构为这一化合物家族的研究开辟了一个新的领域，而这一化合物家族在光电器件和光学存储器领域的应用前景广阔。
• Unraveling Dual Aggregation‐Induced Emission Behavior in Steric‐Hindrance Photochromic System for Super Resolution Imaging
  作者：Hong Yang、Mengqi Li、Chong Li、Qianfu Luo、Ming‐Qiang Zhu、He Tian、Wei‐Hong Zhu

  DOI：10.1002/anie.201909830

  日期：2020.5.25

  Unprecedented dual aggregation-induced emission (AIE) behavior based on a steric-hindrance photochromic system is presented, with incorporation one or two bulky aryl groups, resulting in different flexibleness. The dual AIE behavior of open and closed isomers can be explained by restriction of intramolecular rotation (RIR), restriction of intramolecular vibration (RIV), and intermolecular stacking

  提出了前所未有的基于位阻光致变色系统的双重聚集诱导发射（AIE）行为，其中并入了一个或两个庞大的芳基，从而导致了不同的柔韧性。可以通过限制分子内旋转（RIR），限制分子内振动（RIV）和分子间堆积来解释开放和封闭异构体的双重AIE行为。大体积的苯并噻吩导致旋转受限，从而增加了溶液中开放形式的发射和弱的π-π分子堆积，从而有效地增强了固态的发光性能。通过结合两个大的笨重的苯并噻吩基团，BBTE具有最出色的AIE活性，在交替的紫外线和可见光照射下，薄膜中的高效可逆的自上而下发出的荧光以及出色的抗疲劳性。在超分辨率成像中成功建立了即开即用的光电开关。
• Photochromic diarylethene-containing coordination compounds and the production thereof
  申请人：Yam Wing-Wah Vivian

  公开号：US20070057240A1

  公开（公告）日：2007-03-15

  Diarylethene-containing ligands and their coordination compounds are described. The ligands display photochromism with UV excitation, while the coordination compounds display photochromism with both excitation in the UV region and excitation into lower energy absorption bands characteristic of the coordination compounds, through which the excitation wavelengths for the photocyclization can be extended from λ≦340 nm to wavelengths beyond 470 nm. Switching of the luminescence properties of the compounds has also been achieved through photochromic reactions.

  本文介绍了含有二芳基乙烯基配体及其配位化合物。这些配体在紫外激发下表现出光致变色性质，而配位化合物则在紫外区域和较低能量吸收带中表现出光致变色性质，通过这些能够将光化学反应的激发波长从λ≦340 nm延伸至超过470 nm的波长。此外，还通过光致变色反应实现了化合物发光性质的切换。
• Photochromic diarylethene containing coordination compounds and the production thereof
  申请人：Yam Vivian Wing-Wah

  公开号：US20100137596A1

  公开（公告）日：2010-06-03

  Diarylethene-containing ligands and their coordination compounds are described. The ligands display photochromism with UV excitation, while the coordination compounds display photochromism with both excitation in the UV region and excitation into lower energy absorption bands characteristic of the coordination compounds, through which the excitation wavelengths for the photocyclization can be extended from λ≦340 nm to wavelengths beyond 470 nm. Switching of the luminescence properties of the compounds has also been achieved through photochromic reactions.

  本文描述了含有二芳基乙烯基配体及其配位化合物。这些配体在紫外激发下表现出光致变色性质，而配位化合物则在紫外区域和低能吸收带特征的配位化合物中激发后表现出光致变色性质，通过这种方式，可将光环化的激发波长从λ≦340 nm扩展到超过470 nm的波长。此外，还通过光致反应实现了化合物的发光性质的切换。